September 14, 2022

Building Sales Teams That Thrive w/ Dan McDermott (Vouris)

Nima and Dan McDermott, CMO of Vouris, deep dive into how B2B startup founders should build and structure a high-performing sales team. Spoiler alert — do it by creating a culture of collaboration, not competition.

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The host

Nima Gardideh

President of Pearmill, ex-Head of Product at Taplytics, ex-Head of Mobile at Frank & Oak. YC fellow.

Our guest(s)

Dan McDermott

CMO, Vouris

About this episode

When is the best time a founder should invest in building a sales org? How do you build a team that thrives performance wise but also thrives culturally? Every B2B founder needs to understand how to build high-performing sales team.

We cover all of this and more with Dan McDermott, CMO of Vouris. Dan and his team are experts in scaling strong B2B sales teams.

More highlights include:

  • What the biggest trap is that founders often fall into when building sales teams?
  • How salesy is too salesy? Hint: salesy is too salesy!
  • His philosophy on building a culture of collaboration.
  • Why developing repeatable processes is so important?
  • Why you should avoid internal team competition.

Dan is also the co-host of The Startup Growth Podcast along w/ Vouris founder, Kyle Vamvouris. We love their podcast because it gives you an insiders look at how they help startups with scaling their sales teams.


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[00:00:00] Nima Gardideh: How salesy is too salesy? 

[00:00:02] Dan McDermott: Salesy is too salesy. You don't wanna be salesy. Nobody wants to be salesy. I think that's something we wanna sort of eliminate from the world. I think sales has a bad reputation because of people in the past who have been salesy. So a lot of people, I mean, I'm one of those people who when sales came up, I would think that sales was a dirty word and sort of picture, some typical Hollywood movie used car salesmen type character. And yes, we don't wanna be that. Instead, if we go back to, on both sides, again, marketing, sales, whatever you're doing, everything that you're producing as a company, everything you're doing with customers in some sense should be customer service.

Transcript of the episode

[00:00:40] Nima Gardideh: Hey there, I took a few weeks off to build a hotel at Burning Man. But fortunately, we had recorded a few pods before I left. As I work on getting all of the dust off of my stuff. I'm excited for you to listen to my conversation with Dan McDermott, CMO of Vouris.

[00:01:00] The folks at Vouris specialize in helping startups build high performing B2B sales teams. In our chat, he shares what the biggest trap is that founders often fall into when building sales teams, his philosophy on building a culture of collaboration, why developing repeated processes is so important and how to avoid internal team competition.

[00:01:21] Chatting with Dan was like doing a deep dive into the right and wrong way of building sales teams. It was super fun to learn from him, and I'm very grateful to him for spending the time with me. On a side note, Dan and Vouris founder, Kyle host “The Startup Growth Podcast”. That's packed full of strategies and tips on how to build out great sales teams. Check out their podcast and connect with Dan and Kyle, if you need help, they are both experts in what they do. I'll be releasing my guest appearance on the startup growth podcast later this month. So stay tuned for that.


[00:01:53] All right. Thank you for joining us then. Appreciate you spending the time.

[00:01:58] Dan McDermott: Yeah, absolutely. Nima, great to be here.

[00:02:01] Nima Gardideh: Yeah, thank you. So I'm super excited about this because the main reason I wanted to chat with you all at Vouris was to learn more about sales. Yeah, I think my main general job is to be very, very good at a different form of user acquisition and customer acquisition, which is sort of marketing and paid performance.

[00:02:20] But our own company runs on sales. So, it's something I’ve personally been doing for the company. And recently we've hired a Head of Sales who's been taking over. I'm very curious to look at, first of all, generally sales-led growth and what it takes to run a very strong sales team. And it sounds like you guys have done that plenty of different times for other other companies, which in itself is probably one of those forms of mastery that ends up making you better at it than an internal team and that's how we feel about performance marketing. We feel like we're better than internal teams because that's all we do. 

[00:02:57] Dan McDermott: I mean, that's definitely the case. I totally agree with you there. It's something where if you just, it's one of those things, it's easy to have an idea and know about something, but once you've run through it over and over again, you see the problems, you see the, the sort of the issues pop up and you've, , figure out good ways to handle healthy processes.

[00:03:13] where things are a one size fits all solution and when they're not. And, I think that eventually you also start to collecting people around you that are very good at what they do, where you can kind of bring in the right specialist at the right time. So yes, we feel like we've kind of cracked the code there a little bit but it's also, it's funny, you mentioned that sales and marketing are so vital to pretty much any business. So if you are not doing both, you're probably not doing something right. [Laughs]

[00:03:36] Nima Gardideh: Yeah, there's certainly some forms of businesses that believe they're product lead growth companies. But even those companies end up getting enterprise customers knocking on their door saying, can we talk to a salesperson please? I had one of the co-founders of WebFlow on the podcast a few rounds ago. And he was saying they had to build a sales team because of that. Cuz they had enough enterprise clients saying we wanna pay more. We want SLAs, we want all of this stuff. Why can't we do that? And then they decided that, I guess we need a sales staff and even this is at like many multiple millions of AAR already.

[00:04:13] But that's when they started realizing, oh, they could make a lot more money and then revenue retention just ballooned after that because they were able to have a direct co relationship with all their users that were willing to pay more. 

[00:04:27] Dan McDermott: Yeah, for sure that happens all the time. Actually. There's many examples of, I mean, first of all, look, I mean, I feel like I'm pretty open and gentle when it comes to this kind of stuff. I feel like, Hey, whatever labels you wanna put on it, it's fine. But some people get very tribalistic about, no we're with this type of company and that's it.

[00:04:43] And nothing else is allowed and everybody else is wrong. And I think it's just it's more of, there is usually something to be done now that will help your company grow in some form in some capacity. And if you don't limit yourself to, again, these, these labels and whatnot, you are liable to find something that is very, very good for you at that moment. So much of it is about timing, basically, I think, timing in the market, the product, and it's difficult to say that, it's always gonna be just this one, 1, 2, 3, always forever.

[00:05:11] Nima Gardideh: Yeah. And on that note, I guess, like, this is a good area to start is when do you think it's a good time for people to not be doing sales without the founders being involved? Right. I, at least for us, it took me two and a half years to start working with anyone external, well, maybe two years, anyone external two and a half years, where we were like, okay, we need to hire someone.

[00:05:36] That's not just me doing the pitching and even doing sort of like outbound sales or lead gen. When do you recommend cuz maybe I was, I feel like I was wrong now that we've hired a sales head of salesperson. So I'd love to hear your thoughts on when do you think it's a good time and I'd love to hear also, like what is the mix of companies that you think would need it? Like are the SMB sales people should hire internal sales folks or is it only enterprise? Is it mid-market, is there a framework essentially in your mind?

[00:06:07] Dan McDermott: Actually, before I answer, let me flip it back to you for a second. Why did you choose to, what was the trigger for you to go and say, okay, now I need to hire somebody to do this? 

[00:06:17] Nima Gardideh: That's a good question. So basically effectively, we needed more sales that I thought I could personally handle in terms of, I was maxing out a number of hours per week that I was able to go on pitch calls and I was getting close to that and we had some like top level goals for this year that I was like, well, if we want to get that, we need just literally we need more hours in a day.

[00:06:42] And it's not like I can work harder because there was a, there's a certain number of hours that other people are willing to go on calls with me. It's just, I'm limited by my calendar, which is actually beautiful. Cuz then I can model out what another person could do theoretically. I think David Sacks has that great post on what multiples to use on different like AEs versus SDRs and all this sort of stuff that I use to then model out what it would be like to hire a team. 

[00:07:11] Dan McDermott: Yeah. So I mean that's one of the most common stories that we interact with is that basically it's a company that's doing something, right. They're getting some traction, there's some product market fit there, but the inevitable kind of trap is that the founder it's a founder led-sales, kind of operation the founder then runs out of time.

[00:07:30] The founder also has a job to be doing as founder, as CEO, as in there's many other things to be done there outside of pick up the phone and dialing and selling. Many of the people who come to us basically are in that trap and they're doing a lot of great stuff, but they're hitting that limit in terms of time in terms of energy.

[00:07:48] And then also just in terms of, Hey, it is the right time to scale. Maybe they've recently gotten funding, maybe some trigger event has happened to sort of say like, this is really the time for us to be acting. And we are there to help create the processes to move from being a sort of ad hoc sales org to an actual formal structured sales organization where we have repeatable processes so that you can scale with them.

[00:08:13] And then you also asked, what was there a size issue or what other triggers are there? For us to say now's the time to have a sales team. And, I would go back to sort of what we said before is if you are running into your limits as a founder, if you have specific revenue targets that you feel like you cannot hit otherwise really at any size company, any size organization, that's the time that you should be building your first sales org.

[00:08:42] And what we like to do is often we'll ask the company that we go to sort of say, okay, what is your revenue target? Cause most people have some sort of target in mind, whether or not they have an organization to fulfill that target. Right? And then we can sort of go backwards from there and say, okay, in order to hit this revenue target let's model out backwards, the types of numbers that we need to hit for different types of teams.

[00:09:07] And we do recommend starting with, for example, a couple of SDRs. And if it's the right kind of organization with a bigger market, a couple of AEs and yes, there are ratios for that and you can go in quite deep into that in terms of the modeling outta the numbers. And we do before we work with anybody. 

[00:09:23] Nima Gardideh: Do you also model out, like, do you ask them what their ACV is? And for others that don't know what average customer value is or annual customer value. So then that thing is gonna be more profitable. So you basically get in there immediately and say, well, this is not gonna work out if, if it's low enough or?

[00:09:39] Dan McDermott: Yeah. So part of the reason we do that up front is to number one, just see if it's gonna be a good fit for us but also try to give the people, sometimes people set revenue targets that are kind of a little bit crazy, that are just too high. And then sometimes they're setting revenue targets that are potentially very, very low.

[00:09:57] And by just coming to us, you can just get basically a free call. And we just go through a little bit of a roadmap with you to sort of say like, look this is a realistic number and in order to get there, here's basically the next six months, 12 months of your sales team. Hire these people first, then hire these people, then hire these people.

[00:10:17] Nima Gardideh: Is there some like ratio that you've seen work in terms of like the cost in which it would take you to run the sales team to, , The annual customer value that you need in order for a sales team to work in marketing, you have the it's antiquated, but generally speaking people still think about it, which is a 30% rule.

[00:10:40] The one third rule of, Hey, your CAC to LTV ratio should be one to three and generally speaking, when you have that, your business will work. The answer is like, sometimes that's true, but it turns out to be wrong in a lot of these different instances based on your business model. But, most marketers kind of like to hold that to heart.

[00:10:58] Is there some like heuristic where a founder can think of? Like, should I be more of a marketing organization or a sales organization that you can like easily look at a company and say, well, this is just not gonna be a right fit in terms of building a very large sales team and like one of the main sources of growth. 

[00:11:20] Dan McDermott: So one of the things that I think many people miss when they are trying to model out numbers, let's just stay focused on the sales team specifically. Up front is that they will not take into account all the actual costs that exist when you're looking at basically the ROI on somebody where if I'm going to pay out somebody on commission, then that's gonna factor in a certain amount.

[00:11:42] Right. And then if there, if I'm also paying out commission to multiple people, if there's an SDR involved and AE involved, maybe there's something else in there too. The numbers very easily get mixed up when you suddenly you have a sale, but it's a sale that's not profitable.

[00:11:59] And that's obviously very counterproductive to the entire enterprise here. Right? So, one of the things that we do, yes, we go and model the numbers in, to be specific enough so that this type of a hiring plan and a growth plan is actually gonna remain profitable because we go in and we will set compensation, we will set commission structures, we will set all that stuff so that it protects the profitability of a sale.

[00:12:23] And I think that's an important blind spot that many people don't realize is a real issue. It comes up quite a bit, in terms of a ratio between marketing and sales and how to know whether to choose one or the other. I don't think we've come into a situation where we've ever suggested choosing sales over marketing.

[00:12:42] Usually there's some sort of marketing function either with a dedicated team or person. Many of the companies we work with are quite early on. So it's often somebody wearing a bunch of different hats, but we never say that sales should replace the marketing function completely. We just see, okay, you have an inbound channel for example, and that's great.

[00:13:02] Keep on doing that. We hope that you have a great blog and a great website and a great, , sort of strategy to reach people for sure. But then, , let's also build this out as a function to convert, , and to, , to convert people from, , cold traffic and, , and just reaching out, , to people who we think would be great fits.

[00:13:19] So it's, it's quite a different function and I don't think one should replace the other and we, we've never kind of lined them up to, , to sort of compete directly where it's, , put 50% of your budget here and 50% of your budget here instead. It's like, okay, let's estimate out the costs of what this would be based on your target and build that in a silo effectively.

[00:13:36] And then once the team is built, we don't have to keep that team in the silo completely, but we, we sort of separate the two out is that, ,

[00:13:42] Nima Gardideh: That generally makes sense. And I think if I were a founder, I'd probably do some  mix analysis of like, if I were to spend the next dollar, where should it go? Should it go to more sales staff or on sales versus marketing? And, maybe my mind goes there because I'm a performance marketer. And it's literally how I think, right?

[00:14:01] Where should the next dollar go? And it's a channel mix problem but then why isn't the sales channel? Just part of that same conversation or same thought process, cuz then you can run incremental tests and things like that. there's probably, maybe this is a better question to ask. I was gonna ask this, but are there diminishing returns on more sales people?

[00:14:22] Like if you're, if tomorrow you say I wanna spend five more million dollars on this sales staff, is that the equivalent to the first $5 million I spent on it? Or is there, are there diminishing returns? 

[00:14:37] Dan McDermott: There are diminishing returns and the, I don't think they, they show up for a while necessarily, but depending on the size of your market, you can quite quickly tap the, your premo targets. And if you start to do that and you will eventually kind of cycle down from a plus leads down to weaker and weaker outreach.

[00:14:57] So yes, eventually there's that challenge to be faced in terms of. Having, I mean, you see this all the time where, look at the layoffs that we're kind of currently sort of facing in the tech world. I mean, a lot of that is people hiring too many people, potentially, maybe not expecting the economic downturn.

[00:15:14] And then what happens is you suddenly have a bloated team that you're paying a lot of money for, but then, a market that is not receptive. And I think that's not quite diminishing returns in that sense. It's a mismatched solution for what you have going on. 

[00:15:26] Nima Gardideh: Both of those sound like market saturation, like the market is not accepting it at the vole in which you are trying to accept trying to acquire the customers. Yeah. And it's super similar, I guess, to paid marketing of like, there are diminishing returns because you're basically maxing out the impressions that you could possibly get on the people that are willing to buy your product right now. So then you're doing these longer term sort of things. So, I guess another question around that area is that are there approaches to warming leads up? Cuz there is like the tier one folks that are maybe in the market right now that are willing to buy. Right. I would imagine there is like some adoption curve.

[00:16:07] On the market. It's very similar to paid marketing. We talk about this and there is like 5% of the market is willing to click right now and buy right now. So your first, like, couple hundred thousand dollars of ad spend are probably gonna go towards that part of the market. And they're just ready now.

[00:16:21] And then you have to do all this work to warm up the rest, and it's like a, more of a branding problem, but then it can become a performance marketing problem. Do you do any of that work yourself as the sales lead? Or do you think that's the marketing team's job to slowly warm up those people? So then they're in the periphery and when you reach out to them eventually, with an SDR team, they are more receptive. Like how does that play in together? 

[00:16:47] Dan McDermott: Again, great question. And, yes, you're hitting on one of the topics that a lot of people like to get very frustrated about. So I will hit that for sure. As purely on the sales side, there is a level of warming up in the sense of you're sending out, you’re making cold calls, you're sending out cold emails.

[00:17:05] I'm gonna assume that people maybe do not act on the first on the first, the first touch. The first touch is the most important one, but let's say that they don't act there. If you are following up with the sort of spammy stuff where you're just kind of hammering people with a sale, that's never gonna work.

[00:17:21] So we have borrowed quite a bit from the wider world of, I think this is sales in general actually, but value first marketing. There's an element of that too, in here where we want to lead with, things that are easy to read, things that are actually very hyper relevant to what the prospect is probably thinking about.

[00:17:39] We do a lot of work with messaging and sort of prepping a lot. You would recognize a lot of the same things from marketing where we go through persona building. We go through the problems, the impacts, the pains. Again, I'm a former copywriter, so this is very much my shtick.

[00:17:54] So there is a level of warming up, I would argue in any campaign that we send out or in any sort of multiple touch interaction, whether it's on the phone or email or LinkedIn. So it's a tiny one compared to the marketing side, but it's there. Now in terms of how to interact with a list that is being warmed up by the marketing team. That's a great question. This goes back very much to how the brand wants to be perceived and how, how careful you are about the relationships you, you build out with people. We, on the Vouris side for literally for, for our company, we are very much big believers in if somebody downloads a lead magnet, we better call.

[00:18:30] And, our lead magnets are geared towards founders. And a lot of we know the ones that are sort of, intent, high intent, ones to focus on. And we will call that lead directly, immediately as quickly as possible. And that's something that we do as a very much as a sales org. And we're happy to do that.

[00:18:48] We know that there's other organizations that don't do that, that are very protective of their leads and wanna do a much slower sort of nurture process. And you've gotta know how. What your, who your buyer is and what they expect and what they need. So I think that when it comes to how you're using the marketing team, I think the two sides should be talking to together quite a bit.

[00:19:08] And I think there should be a lot of interaction between the two, but in choosing how quickly, for example, to jump on a marketing lead or when to send a marketing lead, from an NQL, it's basically to become an SQL. You've gotta do a lot of careful strategy with the leadership of the company to make sure that it is everybody is happy to be on brand here.

[00:19:27] So it's a little bit, we will match where that, where the company wants to be, but it's, again, one of these things going back to something I said earlier, being tribalistic about saying this is, you've gotta always call directly every time. That's not true for every company, but if you're in our position, it definitely works well.

[00:19:44] And, yeah, I think it really depends on where you're at and. Aggressive you wanna be with your sale. And then also, how positively the two sides work together internally. Some companies really have a huge split and they never speak to each other between marketing and sales. Whereas the companies that we've seen would be most successful, the two sides are consistently in the same kind of the same room, speaking together quite a bit and sort of saying, Hey, we just came out with this thing.

[00:20:11] We think this is gonna be an excellent lead magnet. And it is high intent, for example, in the buying cycle. Great. Okay. Let's go with this and other times, Hey, why are you calling people that are just downloading this kind of stuff? Or why are you, why are you calling people who are on a welcome auto responder?

[00:20:25] Nima Gardideh: Yeah. I was gonna ask you if there was like a virtuous path and it seems like it's the super collaborative model is the virtuous path of like, okay. Maybe I'll ask you another question, maybe less virtuous, but what is the long term? Greedy strategy. Like what is the one that works over a longer period of time, as opposed to like, maybe we'll hit the goals this quarter, but if we do this for 10 years, it's not gonna work. Like, do you know what I mean? Like how, how salesy is too salesy? What is the balance in your mind?

[00:21:01] Dan McDermott: Salesy is too salesy. [Laughs] You don't wanna be salesy. Nobody wants to be salesy. I think that's something we wanna sort of eliminate from the world. I think, sales has a bad reputation because of people in the past who have been salesy. So a lot of people, I mean, I'm one of those people who, when sales came up, I would think that sales was a dirty word and sort of picture, some typical Hollywood movie of a used car salesmen type, character. And yes, we don't wanna be that. Instead, if we go back to on both sides, again, marketing, sales, whatever you're doing, everything that you're producing as a company, everything you're doing with customers in some sense should be customer service.

[00:21:39] It should be something where you're, you're ethically speaking to people. If somebody says no back off by all means sure thing. I used to have a restaurant and it's very much working digitally. It's very easy to lose the human connection because there it's kind of numbers on a screen or a faceless email, but, even a phone call is, it's more personal, but it's not quite the same thing.

[00:21:59] Whereas in the restaurant world, everybody on the team was there to make the customers, the diners feel at home and I think that's an ethos that I think a lot of organizations should start to adopt and say, look, yes, there are ways to handle everything. And we should be very, very receptive to what the market really wants ultimately, and to really genuinely help people always, always.

[00:22:21] And if we do a good job with this is why the sales team, I think, should always also be talking to marketing and that marketing should want the sales team talking to them is SDRs are often the people who have the most interaction with customers where they're speaking directly. They're sort of, they're your feedback loop.

[00:22:35] And if you can sort of listen to SDRs who have their head screwed on, right. Have some experience there and sort of are listening to customers and saying, guys, what are we doing here every time I say this thing, it lights people up the wrong way and why are we doing this? Great. That's great information.

[00:22:50] Let's drop it. Let's lean into the strengths instead, but when we have these feedback loops and we have a genuine, this sounds a little bit cheesy, but I don't think it is. I think it's real, a genuine passion to solve problems for people. Then we can create the entire system to be hopefully never salesy and always helpful pipe dream, maybe, but, but it's a good one.

[00:23:10] Nima Gardideh: This obviously makes sense to me. And, and generally speaking, I also believe it on the engineering side as well, where I think it happens a lot in engineering org where disconnected from the user. So I encourage our engineers to be on calls with customers to get an understanding of what's going on.

[00:23:26] It's not just the PMs, right. Of like, Hey, here's the problems we're solving. Here's where we're bothering people. And we're, we're being like a net negative force. Can you actually, so you, we've, I'm realizing we've used some acronyms. Let's actually talk about what a sales team looks like. What is an SDR?What is an AE? What are their respective jobs in your opinion? 

[00:23:49] Dan McDermott: Can I just add one quick thing to the last thing we talked the last point real quick, sorry. But I think that, a lot of times when we speak about sales or marketing teams, or even company growth, we look at a lot of milestones and just sort of look at the results and not the, the processes in a sense where, I think you'd agree of the processes are the more important one to look at.

[00:24:11] But I think one of the ways we try to look at things is as this, consistent human capital growth, where you're really training your team to be better. And by creating a lot of these feedback loops and collaborating on messaging together as a team, get the CEO to come down and write something.

[00:24:29] You had an SDR to come in and write something, where do they, where are they completely off? Where are they together? This iterative process every week? Are we getting 1% better? Is something where I think that's where the true improvement comes. So, and I think that's where you ultimately become better at serving your customers. So sorry. They just wanted to close off on that.

[00:24:47] Nima Gardideh: I was going to bring you back to this part of mastery, so let's, let's get to that right after, but just to like define the, the terms we've been talking about, , yeah, just quickly walk us through what is an SDR? What is an AE? Is that the only two roles that you should care about? Are there more?

[00:25:04] Dan McDermott: An SDR is a sales development representative. And it's a position where they are the people doing the cold calls. They're the people doing the prospecting. So cold calls, cold emails, cold LinkedIn. It's often an SDR who's reaching out to you. And an AE is somebody who's an account executive and they're the person who is doing the demo and essentially closing the deal and making the sale.

[00:25:26] And then there's also on the team, often a sales manager and sometimes a VP of sales. And depending on the team, your leadership might look a little bit different in there. So there are also a SDR managers, sometimes there's sales coaches who are also involved, but for the most part it's SDS, AEs sales manager, VP, and then company leadership.

[00:25:48] Nima Gardideh: And do the SDRs report to the sales manager? They report to the AEs? Is there a mix?

[00:25:54] Dan McDermott: This is very different across the board for different companies. So often since we are building the first team, we will, the first couple people that we bring in are often a couple of SDRs, two SDRs and one AE, for example. And at that point there is no sales manager often. And if that, if that's the case, then they report to us. And then, also to their company leadership directly, once a sales manager is put in place, they're the person that they report to.

[00:26:18] Nima Gardideh: Oh, interesting. So an AE is still an individual contributor in your model where there's a sales manager.

[00:26:25] Dan McDermott: Yes. And sometimes an AE is a full cycle salesperson where they're doing the prospecting and the closing, depending on the nature of the team.

[00:26:32] Nima Gardideh: And how do you fit in organizationally? And maybe you don't do this. I'm curious when there are more technical products where you need sort of like a sales engineer, if you were to design the org, I guess, how do you think about it on your end and versus if there was an internal team, internal sales team, how would you organize people?

[00:26:54] Dan McDermott: That's interesting. I think the idea it to simplifying your messaging down to a point where it's easy for anybody on the team to sell your product. Let's put it that way. So I think that, I think that's the responsibility of people like us, but also the company leadership, essentially to have something where we have a message that is easy to understand by our customers, our prospects, and is simple enough to communicate by the people who we hire.

[00:27:24] And I think that's where, if you have something more technical by all means maybe the AE has the, sort of, the experience needed to walk through, exactly how the product works. That's usually saved for a demo, I think, best and where you have more direct communication. But I think every person on the team should be able to handle at least the basics of how something works and how a problem is solved by what we. 

[00:27:50] Nima Gardideh: Yeah, I think I generally agree with you. There's probably a subset of the market that are like selling Def tools. That just doesn't work with. Cuz they're speaking to like a CTO who was asking you about does your API support X, Y, and Z. And can you show me a demo that you use that API? And I've just seen it work where like, I think data doc does this, for instance, where their sales engineers within like a trio of an AE and SDR sales engineer and they work together to like build demos quickly, the engineer will go and put up like an example of the product being used for that specific use case.

[00:28:23] Cuz they're all like API companies. So there is no interface. Right. So in order to do that, so, it seems like it works to some extent when, at least in those types of instances but maybe you're right in that if they had done their jobs very well, the AE would be able to do it without, 

[00:28:39] Dan McDermott: For the most part, when an SDR makes a cold call to somebody in a two to five minute conversation with somebody, can they hold their own with enough technical knowledge to sort of surpass expectations.

[00:28:50] And, and I think the answer is that should be the case most when I was selling solar products, I definitely did not have the technical know how to give it necessarily like a scientific presentation. But, I knew my product. I knew the competing products. I knew the general, the very simple 1, 2, 3 of how they worked.

[00:29:11] And I knew the major problems and questions that the person was gonna ask around like, wait, budget, have time these kinds of things. And then when I don't know what to do, and this is something that we always advise our SDRs to do, if you don't know what to do, say you don't know, and just bring in the person and say, I'll connect you directly with our CEO, for example, or our CTO or somebody who's, who really has the, the capability to have that in depth conversation with you. 

[00:29:33] Nima Gardideh: Yeah, I think that's probably the case in which you would need an engineer on staff to some extent. And maybe it's not like for an AE and SDR, you need one engineer. Maybe it's like every 10 pairs you need one engineer or something like that, where you would need the help in these companies actually don't know.

[00:29:51] Right. I'm just curious about it. And, there's this woman, Diane Green that built VMware who talked about a sales engineer being paired with an SDR and an AE that made them grow in the, in their rate in which they did. So it was just a curious thought. 

[00:30:06] Dan McDermott: That's a great idea. 

[00:30:08] Nima Gardideh: Yeah, I think it's an interesting model, right. Especially when he's like super technical products, but otherwise I think you're right in that it's more, more or less a. Understanding training problem, where you just make sure that you're a steer and AE understands the problem space, the specs of your product, how it solves the problem in a meaningful way. 

[00:30:30] Dan McDermott: I mean one way to counteract that or to sort of speed up the training process is to hire within and from the industry. So, I know of an architecture SaaS platform, for example, and they hired architects to be their sales people. And, first of all, the amount of trust that builds with people right away and the amoun, of sort of industry jargon that you can speak, because you've just been in the industry for 10 years as that role is quite powerful.

[00:30:59] So even in this market where, again, there are layoffs and there are all kinds of things happening, but, sometimes just hiring from that, from the market that you want to target is a great way to also get a sense of, are we saying the right things? Are we being weird? Are we, am I hitting the right tone? So yeah, and also the technical know how. 

[00:31:16] Nima Gardideh: Do you think that it's easier to teach the sales part than it is to teach the technical parts in that example?

[00:31:24] Dan McDermott: Oh, great question. I, and I think it really depends on the person, so great coaches need to know how to respond to teams. And one person on a team might need a little bit of tough love, for example, and the other person you can't do that, it's just gonna break their confidence completely.

[00:31:39] So, the same thing goes for, is it technical know how, or is it a sales thing? And I think that different people have different blockers in place. I think giving somebody technical training is quite straightforward and it's quite objective. Like, can you answer this quiz at the end of this onboarding session?

[00:31:55] Do you know this thing works? And the answer's probably yes. You go away and study it. I think everybody could be onboard with that in a matter of weeks on the sales. If you don't have that little feedback loop, you can get stuck pretty easily because there are all kinds of, instead of, book based sort of academic, , barriers, information barriers, there are things like confidence, barriers, and mindset barriers, and things like empathy, barriers.

[00:32:20] So getting somebody a little bit better trained up on their sales skills is often, I think a little bit more subtle, not necessarily more difficult, but you have to know how to listen to that person and understand, how to pick out their strengths and weaknesses and then how to then coach them up.

[00:32:35] So, they're both important, but I think some people struggle with the sales side a little bit more. 

[00:32:41] Nima Gardideh: The rubric seems to be less definable, almost of like…. 

[00:32:45] Dan McDermott: It's a lot softer. It's one of these, yeah. 

[00:32:47] Nima Gardideh: I can relate to that. I think that's like, that was like an area in which I would say I struggled at first trying to hire a salesperson because I was looking for my versions of those things. Right. I'm like, oh, I do it this way, but doesn't mean it's the only way to do it. And, we've not found someone who's arguably better at, than I am, which has, which has been fun. 

[00:33:09] Dan McDermott: Great. That's the goal? 

[00:33:10] Nima Gardideh: I'd love to walk, like, I guess hear about the process part. Right. And for context, I think you're right in that I totally believe the process is much more important than anything else. We talk about it internally where we want our job is to learn things, not to get the CAC goal that our clients want.

[00:33:31] And in fact, we also tell our clients the same thing, right? The success metric is learning meaningful things at the right cadence. Right. Ultimately that will, and it has so far for us lead to success. It's just harder to wrap your mind around when one week it doesn't look good or like five weeks in a row.

[00:33:56] It doesn't look good. But what we've done in those five weeks is that we've crossed out so many things that we know now will work. So what, yeah, first of all, like what is the general process, if you were to sort of simplify it and then I want to hear, talk about how you instill the process within the team and how you communicated with the clients and making sure founders who want the sale yesterday, understand that it takes, it takes time. 

[00:34:22] Dan McDermott: Sure. And, I think that, let me walk you through, like, I guess what, what we do and I think it's a pretty healthy way to build. And you'll probably, again, relate to a lot of this from the performance side because it is iterative and loop based, I suppose. So we approach things from a three phase structure.

[00:34:40] And what we'll do is in phase one, we will sit down with the executive team and just get everything in one place to do with messaging strategy, target market, and sort of get a high level thing, but written down on one place so that everybody is, is clear. Often what we'll find is there's a lot of misalignment between different people, because you just assume that we all say it the same way and then things get shifted, big differences happen.

[00:35:03] So it's a great exercise just to get alignment on all the key things that you should have in terms of the product knowledge, the brand knowledge and essentially what you wanna communicate to your prospects and your customers. Then we, once we have everything in good shape, oh, and we also do our, our roadmap, session where we look at the, your target revenue, and then we work backwards to give you a plan to build that.

[00:35:25] And then in phase two, we go out and we start to build the team with you. And one way we do that, we're not traditional recruiters in a sense, but we will go out and find talent and do a lot of the vetting and the filtering. So instead of just throwing a company here's a hundred sales people, good luck.

[00:35:41] We will really kind of, we'll just send over one person. The, this is maybe two, possibly we've done three in the past, but one or two people at a time and sort of say, look, this is the best of the best. Go for it or don't, but it's their choice in the end, but we will then sit and actually find the right people hand, pick them and put them on the team.

[00:35:59] And like I said, we're usually building the first sales team usually. So it's often just two or three people at a time. And in that second phase, we will then start to implement all the processes that we have in our tool. It's like getting the first email campaign set up and running, getting their cold call script set up and running and basically getting some results back and what we wanna be doing again from the performance marketing side, you might, feel good about this part is we're setting a baseline.

[00:36:24] We wanna see what is working and what is, what are the numbers telling us? What is the market telling us in reality and not just up here where we're in kind of Lala land and based on that, we will eventually move into phase three, which is just pure coaching. And over time we will work with the executive.

[00:36:42] A little bit less directly. And then, with the individual reps more directly, so that by the end of the six month process that we have, we will have a, everybody participating in essentially a coaching cycle where we're listening to calls, we're reviewing emails. Were if somebody's stuck on something specific, we'll work through a difficult prospect with them.

[00:37:01] We'll look through a difficult profile for example, and go through exercises basically every week we have daily sessions where we will sit down with the team and. For example on Thursdays, I teach a copywriting session. Everybody comes to that from the team, but then we have an SDR session, an AE session leadership session, and we will give very focused coaching feedback.

[00:37:23] So over time, the idea is we set the strategy we recruit and we build the team and the processes with the team and with the client. And then we will go off and coach the reps to hopefully make them all very good at their jobs. And we have almost, I think we might have had one or two people leave their positions across all clients. For the most part, the people who we hire, they stay and they get pretty good at what they do.

[00:37:46] Nima Gardideh: Interesting. So I'm hearing like two or tool loops, post sort of launch. There is one at the individual level. How can I make sure that this sales rep and this SDR and this AE is very good and we're getting better and better over time, that's a loop. And then there is like an overall, how is this messaging working overall across all these folks and how is it sort of landing?

[00:38:09] So there is like a human loop and then there is like a more abstract, how are we messaging our product and our sales strategy to the market loop?

[00:38:19] Dan McDermott: And I think there's a third one. And it's to do with strategy or timing maybe. And it's to do with basically. Is now the right time to shift into a different target market, is now the right time to like add another persona. Cuz usually these companies that we're working with have multiple tracks.

[00:38:36] And what we do is we sort of say, look, let's isolate one, let's get, let's get one nail down. And then, over time, we are gonna assume that we're gonna get better at this one. And then also, add a new one and the new one you've, you can't just copy, paste everything over and change the title.

[00:38:51] And just say it's all the same stuff. You were talking about CTOs before CTOs have very different concerns than a CEO, for example, or a CMO or a chief information security officer, for example, a CSO they're the most fun because they are very laser focused on a certain set of metrics that nobody else really is in the same way. So what's keeping that person up at night. Rebuild that strategy. So I think it's a, yeah, it's those three loops.

[00:39:17] Nima Gardideh: So it's like a persona slash even like a market segment that you would want to go through some loop in iterating over, or like adding them. It sounds like it's more around, Hey, we're gonna expand to this one now because we figured this, hopefully you figured the first one out and then you kind of going onto the second and the third and so on and so forth.

[00:39:34] Dan McDermott: I mean, we're also there to be honest too. And if something is not working, maybe it's time to drop it. Maybe it's time to just say, look, I, we've done this with a couple thousand people here and it's not really working. It's time to drop this thing and, and move resources to a more effective place greener pastures.

[00:39:49] Nima Gardideh: Yeah, that makes a lot of sense. And that that's always been like an area for me. I think that I was scared of doing outbound is what if I burn all the leads, not knowing what I'm doing. And I think I had to get over that. I was like the first thing I had to get over it. And it's an interesting area of when you, as you mentioned earlier, So much of it is like a mindset problem of how you think about it.

[00:40:14] And I'm super fortunate to have been in therapy effectively. And, I did all of that in therapy and I think a sales coach would have probably done the same for me like, well, just send the first 10 out and get some data and then iterate on it. And, I finally enough, I like got over that in therapy of like, maybe I should just send the first 10 emails that, and I could have done, I've done some sales coaching, but not around these emotional problems. It's more around how to think about these things. And how do yeah, how much are you thinking your therapists than sales coach coaches? 

[00:40:48] Dan McDermott: Oh, geez. That's, that's funny. I think, I'm very big into the performance world. I, think this is an area that, you mentioned mastery. I'm fascinated by this space. I grew up playing sports, so that's often my lens on the world, but, most of the jobs that I've had in the past, especially when you look at either marketing or sales or whatever, I view it as a performance thing and a skill to be learned.

[00:41:11] And, the way that I've read about good coaching is that it's even good self coaching. It's about understanding the right time to come in with the right type of feedback. So for example, if you've just had a rough sales call and you just got sworn at, or that you hung up, but you may made to feel not so great about yourself.

[00:41:30] Now's not probably the right time to come on hard on yourself and be like, oh my God, what could I have done better? Now's the time to probably. Breathe a little, so you've gotta play that for yourself. Take a break, be like, okay, it's okay. I'm gonna take a walk, take a whatever. I'm not gonna pay attention to it too much.

[00:41:43] Just it's the nurturing side of things. Then you can come back later with a more rational kind of, Xs and Os thing. Okay, next time I should do this. And just balance out between the nurture and then the strict kind of feedback. The rational cold stuff. And I think that at some level, again, very much not a therapist here, but I have been through therapy and I think that every good coach that I've ever had has some little element yes.

[00:42:12] Of helping you unlock some things for, I hesitate to say therapy, but potentially at least self coaching. And, they give you the framework and the tools to help you. I dunno if you're familiar with the book, deliberate practice or sorry, “Peak”by Anders Ericsson. He's the guy behind Malcolm Gladwell's “10,000 Hours Rule”

[00:42:31] So, Ericsson is actually the person who came up with that, but it's not just 10,000 hours of practice. It's 10,000 hours of deliberate practice makes you a master at something. And that means get a coach where you can get this a person just say, so why do you think you did that? How did you feel about that and ask these kind of open-ended questions to help people get, challenge and think free, spin the ideas around, in their own head, productively and healthily, and then give them yes.

[00:42:57] At the right times more direct feedback and say, Hey look, I noticed that you did this maybe next time try saying this instead. Here's why I think that's the case. Give them a logical, rational reason for that. And never just criticize, I mean, say, give them an alternative thing to do to make it better.

[00:43:12] So in that sense, yes. I think there's a little bit of therapy going on. There's a little bit of constructive criticism maybe, but overall it's really about understanding the person you're looking at as a part of your team, somebody who's there for the long run. And I feel like some sometimes especially entry level sales people get burned like this by, oh, replaceable, let me just get rid of them.

[00:43:31] And I think that most people are really coachable and really, they show up with the right kind of energy dedication. They just need a little bit of help to unlock some behavioral stuff to get them a little bit more confident. get them speaking on the phone. And we just had our own SDR actually finish up his first month.

[00:43:47] And I mean, I turned around, just told him, I was like, look, your first month in the seat, you've made more calls to customers than most founders ever do. That's pretty powerful. So let's keep going with this little things like that, I think are, are very important to always keep it positive, but also realistic.

[00:44:03] And, that's why we also have a very strong focus on numbers and data. And we always come back our SDRs, and all the client SDRs too. They track their activities every single day and we get them to write it down manually because, yes you can find all that stuff in any tool. It's all automated, but put it down manually. You'll see, again, feedback loops. I keep saying that, but I, you create your own feedback loops that way.

[00:44:25] Nima Gardideh: Yeah. There's an interesting thing. I was talking to a friend over the weekend. Who's trying to get really good at ops and she was saying, oh, my CEO's asking for all this like information about activities and task management and getting updates on things. And so my immediate thought was, oh, why don't you just expose your internal notes?

[00:44:48] And she didn't have the internal notes. And so we, I started talking about rituals. You gotta build your own internal structure on how to do things and how to care about things. So I want you to write out all the things for yourself first and the symptom is that you are not doing it. So then they're not finding out about it mostly because you don't have your own internal structure.

[00:45:08] So that sounds super familiar and this is how, like, I think everyone needs to get good at ops is building in your own internal loops that coincides with what the company and what the organization's loops are like. And then, so you can fall into it, but it's easier said than done and it sounds like this coaching that you guys do is just this han aspect of, Hey, we're just going to think of you.

[00:45:34] And, I generally used to dislike the sports analogies, but because I did not grow up playing sports. So I actually don't know what it's like to be coached well from a sports coach and. As I've grown older and spoken to people who keep drawing the analogies and have gotten, dug into it.

[00:45:54] It sounds like what you're talking about. It's like, Hey, I'm basically helping you co like regulate better because I am noticing things over a longer time period as an outsider, and it's super helpful. Right. That's super cool. So you have these like three different loops going on. Some of it is, I guess, because there is like the performance aspect of it. There was a very clear indicator of failure and success and you are saying that, when do you say this is not working out to someone.

[00:46:30] Dan McDermott: Yeah. That's a great, again a great question. It's a tough one. And it's, it's one where it will come up inevitably. It will come up and I think you've gotta look back at that tracking sheet. I think that's one of the key indicators is if somebody is. Is dropping the ball on some of their self tracking.

[00:46:46] That's often sort of an indicate that something's, there's something up and either, oh, I'm too good for it. I don't need to do that kind of stuff. Okay. Maybe that happens sometimes, but often, often what, and that's still the wrong answer by the way. But often case, I think it is disillusionment, distraction, people who just don't wanna be at that job.

[00:47:06] The things that start to fall away first is, this data entry, this daily tracking sort of thing, and the people who are invested in it, on the other hand, they show up to things. And, so it's not that you're, for example, with Voris, you're not obligated to come to our daily coaching sessions and whatnot, but, it's something where the people who are dedicated, yes, they do show up for their, for their stuff and they show up ready and they show up, once somebody stops working on themself, And just start showing up to the job.

[00:47:34] I think that's a little bit of a danger in any sort of performance based skill. That could be true for, again, I go back to the restaurant stuff. Somebody's just going through the motions. They don't really wanna be there. And if somebody is actually working and showing a chef who is constantly coming up with new dishes and whatnot, that's a great way to see there's some sort of dedication, a willingness to throw ideas at the wall and be told, no, they don't work, but keep on coming back.

[00:47:58] And once you lose that, I think it's a, it's not necessarily totally black and white, but, I think that's, one of the indicators to me where I get a little bit nervous. If I see somebody not reporting back on the very basics of what they're doing. 

[00:48:10] Nima Gardideh: Yeah. And I think the way, like the thought came up, as you said, that is this, you are looking for some form of consistency, cuz that's a, a big portion of how this thing works is. Not just showing up, but being in the same frame of mind constantly throughout your day. So then you're applying all the learnings that you've had before.

[00:48:30] One part of this thing I'm curious about is how much do you ask people to live healthy lives? Because at least to me a huge indicator for how good I am at being ritualistic and following what I know would work. If I follow it, am I sleeping well, am I eating well and is my personal life in a stable state?

[00:48:56] Like, do you find that that's part of your job as sales managers? , or just generally managers and how, again, how deep do you go there? How do you talk about it even? 

[00:49:08] Dan McDermott: Yeah, I think it's, it's something that's also a wider thing in the sales world that is thankfully being spoken about more now. And it's one where it's, I think if you rewind even 10 years ago, I was gonna say 20 or 30, but even just 10 years ago, maybe even five years ago.

[00:49:22] It's a lot of it is an unhealthy culture where it's sort of saying you gotta kind of burn through burnout, but you've gotta kind of burn through all your reserves to just be showing up every day and do more and do more and do more and get paid more and get paid more. And that kind of stuff is obviously, it's not sustainable, it's not healthy and it's not, it's not enjoyable to be around.

[00:49:44] I think so if you're building that type of an organization, there's many organizations out there that do this, unfortunately, but I think that one way to make it a little bit. To avoid that is in the community. I mentioned that our training is a community first platform. And the reason that we do that is that we can hold regular events from outsiders who will come in and talk about, for example, mental health, or come in and talk about how to set up, you mentioned bedtime routine.

[00:50:08] We haven't done that yet, but I think sleep is a huge part of performance for literally anything that you do. So, we are not necessarily always the experts. I will bring it up as often as I can, about basically like, Hey, how's it going? Because I mean, I'll often just have one on ones with people and just sort of say, is everything okay?

[00:50:26] Are you doing okay? And if, excuse me, if they're not, or if , either physically sick or feeling a little bit out of it on our own team, we will tell them, take the day off, relax, just get yourself. Right. Don't there's no pressure here to be, again, we're not looking necessarily at like, you have to be picking up the phone like this, like, a robot.

[00:50:46] But it's one that I think we could probably get even better at. And I think that the way there that I'm most excited about is getting more experts in who are now talking about this directly to salespeople. And we do that through our community, but also like if, if we do webinars in the future, we have somebody coming in on, I believe, end of August, who will be, who's there to talk about mindset and  how to sustain a positive and healthy one without, without driving yourself crazy and he's really good at what he does. I'm really excited to,speak with him. 

[00:51:14] Nima Gardideh: Yeah, that's super cool. That makes a lot of sense, especially because it does really feel like a high performance sport, like sales does to me, I think, I'm in an interesting way, super grateful to have learned how to do it because I had to then go back and say, oh, my old, like, let's say, if I'm using Paul, Graham's sort of words of the maker schedule that I had.

[00:51:36] And for context, that I'm an engineer. So I, most of my career was sleeping super late, waking up late, and going through that schedule. And then I've completely shifted over the last two years where I'm waking up automatically without an alarm. In fact, if I'm waking up with an alarm, I consider that to be a bad day because I've already ruined my rhythm.

[00:52:01] And I like to have a shutdown sequence after a certain hour during the work week. Like I'm super methodical because I've learned that that's what works in my role as a growth person effectively. Although I do run our engineering team, but, I don't code into the night anymore. It's just like, I've had to learn how to do that and fit it in the day.

[00:52:23] Dan McDermott: Do you have a specific sort of ritual that you do around journaling or around that kind of, that kind of, , , sort of self-examination.

[00:52:30] Nima Gardideh: Yeah. I have a weekly, so there's two forms of journaling. I do. I have a work journal that's once a week, I do that on Monday mornings. And then I have what I call my emotional journal and that happens more sporadically, but usually at least once a week, if not more. And it's mostly around, like there are acute problems that I want to think about.

[00:52:55] So then I'll jump into it. And then I have therapy once a week and I climb every day and that's kind of my resetting sort of mode where after work, I climb for an hour, sometimes not everyday the whole hour I've learned, cuz I'm trying to also get good at climbing. And, the thing that happens if you climb every day is that your muscles are always sore, so you can't actually get better at it.

[00:53:17] So I've been stuck in the same state for months, and talking about mastery, right? You have to be comfortable with that. But the second thing is I have to actually take breaks. But it is a super helpful sort of meditative thing to do. And I do it solo. I don't do it with other people. I don't like talking at the climbing gym where a lot of people wanna talk to me. I'm like, sorry, I'm not, I'm not here for that. [Laughs]

[00:53:40] Dan McDermott: That's great. I mean, isn't it funny how many things are analogous here? Like when, when we're talking about the idea of skill development or of life improvement or in terms of just getting healthier, even getting healthy, these are holistic things with many moving parts, and you've gotta be able to learn and develop your own kind of routines around this.

[00:53:56] So, one thing that we did is we actually published an SDR journal. Like we called it SDR mastery journal, where yes, it is about tracking your hard numbers for the activities that day. But then every day there's a space to kind of come in and be like, okay, blank page. How do I feel? Just a, your diary section?

[00:54:12] How do I, how did I feel about today? Just open-ended and then we finished that off with saying, okay, name one strong thing that you did that day and one week thing. And then the goal for tomorrow is just to address that week. Again, we create these little loops to keep somebody just always working on something that's digestively actionable and something that they can work on, but also balance out a few of the other things, hopefully to de-stress and vent.

[00:54:41] And I mean, I have this sleep disorder called narcolepsy and it's for me, one of the biggest levers that I ever pulled was getting my sleep in better shape. But for other people, it's a struggle with being told no, at some point. And then also you're a human being, you change over time.

[00:54:58] So I think having these structures in place where you're able to self-examine in a healthy way, six months down the road, you might have a different challenge a year down the road. You might have a different challenge. That's part of the nature of human growth. So I think these things are very important for like, like you said, any sort of performance skill, but probably just life in general too, to be totally honest.

[00:55:18] Nima Gardideh: Yeah, it's funny. I got some pushback from my same friend I was talking about ops with and she was saying, oh, that feels like very rigid in the way you run your life. And I think there is like something to that. There is probably some virtue around being very spontaneous. But what it gives me is this ability to be absolutely and completely present. 

[00:55:43] When I'm not at work, there is so much structure running around me and the way I like to conduct myself at work and how my own household runs, that when I'm at a dinner with friends, there is no other like loop running. Oh, did I remember to send this email out or did that thing happened?

[00:56:04] None of that is happening. There is no noise. I am just there. Right. So, I think that was the reasoning that that's actually what I used in order to say, I need to change because I'm not present after hours and it was something I also saw in my father, cuz he was also an entrepreneur growing up.

[00:56:23] He wasn't really able to be fully present after he would come back from work and most of the conversations were around work. For him because of that, cuz he wasn't able to disconnect and it's something my mother would always tell me for years on, like you gotta stop working and she'd call me at like eight and I'd be at the office or something.

[00:56:42] She's like, why are you at the office? And so yeah, I completely relate to this and, and it's unfortunately way easier set than done. And when I was telling her, it took me years to get to this state, I would say I've been attempting to get to this rhythm for six years and succeeded the last two years.

[00:57:04] Right. So four years of working on it. And then the last couple years I've been basically on it very well. But it's an interesting problem and what we do and, and I wonder, so you're hosting these events where people are coming in and, and there is now processes in which you're building mastery components in your organization. Are there philosophical conversations you're having with your team. Is there, like, do you ask them to read some sort of mastery book? What are the other things you're doing there? 

[00:57:40] Dan McDermott: Yes, all the time. I mean, we're, I think as a team we're pretty, pretty active readers both deep and wide depending on who you're speaking to at the right time. But, so one thing that we've done in the past, yes, is to actually our last giveaway was all about, was a book based giveaway, the best sales books that ourselves, and then several other teams from different different software companies had chosen.

[00:58:01] , and , with each book came a little bit of a reasons why. So we don't have a book club technically yet, but it's something that I have been thinking about installing. But instead so far, what we've been doing is, essentially training with references to specific books to read.

[00:58:20] So for example, I will occasionally dip into a client's marketing team to say hello. And, one of the things that I did with one team was to turn them onto “Jobs To Be Done” handbook. And, I dunno if you're familiar with that. So little things like that, where it's like, okay, let's take a practical book, or the mom test and sort of, read it together and tell me your shoot me your takeaways at the end of the month.

[00:58:46] And then we'll have a little conversation about that. For example, on a wider philosophical level, we do a ton of, again, different angles here. Number one would be goal setting sessions. So we do those all the time and sort of ask, why are you setting these types of goals? Just think about the goal that your bigger why, and really challenge yourself on it.

[00:59:08] And we'll work, through a structured process with people, every level of the team on these goal setting days, every month. And then in an internally just divorce, we're constantly having conversations, little argents, sometimes little things about where we wanna be as a team.

[00:59:24] But, the philosophical part of it is probably one of the biggest things, Where do we fall in this matrix of companies out there telling you to go cold call and it's one where it's very, it's a shifting market. And I think you have to constantly look at it as such, it's always gonna be shifting.

[00:59:42] So if you are able to approach this as something where we're trying to empower people to really be the best versions of themselves, and I really mean that and truly serve their customers. And again, I really mean that. Then from there all other philosophical, philosophical ideas of, sort of, how we get there become almost secondary to me.

[00:59:59] And as long as we're getting people to really buy into those two concepts, I'm gonna be better. And then I'm also gonna serve my customers the best possible way, how we get there is just, then maybe a little bit about, it becomes pick your, pick your, your topic of the day and we can talk from that point to anywhere. 

[01:00:16] Nima Gardideh: Yeah, I like that a lot. And it's cuz there's, what is that phrase? There's many ways to skin a cat, which I don't understand. Why would you wanna skin a cat? [Laughs] But it falls within this point of like, there's definitely different ways, like climbing and the way I journal and all this sort of stuff is just one format.

[01:00:33] My partner is an Ashtangi and she does like an hour of yoga every day, for instance, and super similar mastery mindset. And it works for her cuz it's super meditative at the same time, same word climbing for me, super meditative. And for some reason I used to do Vipasana but combining the physical aspect just made it better for me.

[01:00:53] And so I guess like let's talk about competition because there is some of this aspect of like, people wanting to become masters of their craft obviously makes it such that they can become better over time and get the job done in the way that is possible. But there is like other levers at your disposal.

[01:01:19] And it feels like to me, competition is at least like a very common one used in sales team. So given your mindset of mastery, how do you fit that in? Do you fit that in at all? do you use it mostly as comparison tools to say, Hey, this is what's possible. What is the messaging approach behind competition in teams? 

[01:01:42] Dan McDermott: Yeah, that's again, I love this question because it's very much what stuff that we care about deeply. I think the competition, as a thing, as a word, as an idea by itself is neither negative nor positive. It's a neutral concept. It's just, it is there. I think it comes back to competition within culture.

[01:02:02] If you have a culture that is driven towards, it's a zero s game, it's cutthroat it's me versus everybody else. It's either I get paid or the other person, and we never share stuff. Then by nature, competition will be extremely unhealthy and it'll just become this very, kind of caustic thing where people are just out to just, I'll just show up, try to be better and just hide my stuff from everybody else.

[01:02:24] Whereas if you have a positive team culture, and you're really there to sort of say like, look, if I do better, you do better. And let me help you. And let me come to you with my question, because I know you're really good at this. And, I'm really good at this. Let's have a conversation when we have teams that build a culture like that.

[01:02:40] That's open, that's question based. That's collaborative. As I mentioned before with even the marketing teams coming in with sales, when you build a collaborative team culture, then competition becomes this beautiful driving force to become better as a group. And that's where the best teams that I can think of.

[01:02:59] I can think of at least five off the top of my head, where I know that they will actively ask each other for help first, before going to leadership. And before coming to us and they will, they will go directly and sort of say, Hey, what? Mike has the best CTAs. I dunno, I love his CTAs. People always get talk about how he closes off his emails and they always reply.

[01:03:19] I want to, they'll go to Mike cuz Mike has shared his stuff. And the way that you get there, I think is the way you can foster this very directly by leadership. We try to do this as well, but you also do this by creating routines for people. So it's not sharing just doesn't naturally happen by itself magically.

[01:03:35] But if you say, Hey look folks, every Friday, let's show up and have a little bit of conversation together and let's grab what was your best email this week? Let's look at him and out of this session, let's grab the best email from the session and sort of like a reward again. Let's go back to Mike for a second there, right?

[01:03:50] And say, Hey, Mike's was the best. This is gonna get saved. And people in the future are gonna come and it's even gonna get put into our onboarding process and our training process. And when you're, when you are onboarded onto a team where you are learning directly from other people on the team, in addition to training methodology, in addition to your leadership, that sort of creates the expectation that, Hey, I can contribute my best stuff.

[01:04:11] I can learn from other people here. And then honestly, I don't see competition being even an issue because SDR is an AE, especially they, the better the conversation that an SDR starts, the easier an AE life is gonna be the better an AE does to sort of follow up and do a tiny bit of customer service by checking in on the customer.

[01:04:28] Once they become a paying customer, that little bit, that little touch will do wonders for retention and for, , referrals. So I think collaborative, positive culture is something that's a very kind of vague fluffy term, but there are ways to build it. And it's one where if you do it right, that's where competition becomes a wanted asset almost.

[01:04:48] Nima Gardideh: Yeah, I love that. Look, I think I personally historically thought of competition as just generally negative. But again, I think it goes back to not having been part of sports teams that also see it as super fun and additive as opposed to something that be negative for you. And now I have, I also think you need you to learn how to have internal competition and at the moment you have internal competition, then it become it can be very fun and easy with other people.

[01:05:18] , and the cultural aspect I think is like probably the biggest lever you have access to as a founder or leader. The area in which I'm curious about, and I do want to get into this other part in a second, which is, marketing teams and organizational design when it comes to those two.

[01:05:39] But the last question I have for you is a lot of what we talked about just now is limited on some prerequisite almost, which is you need to, as an individual, who's trying to get better at doing what they do to be beyond a certain level of like mental ability or out of, what people commonly call Maslow's hierarchy of needs, which by the way, is not, is not a hierarchy if you read Maslow, but that was like completely created by management books. [Laughs]

[01:06:14] But yeah, it's a funny one, but it does make it's the easiest way to convey what he was talking about. But the point is that you have all these needs that have nothing to, like, if you don't have those met to some extent, none of what we just talked about matters, like you're just not gonna be able to have this loop in your mind of improving or even it's not that you're not able to improve.

[01:06:37] Maybe it's the ultimate thing that you're looking for and correct me if I'm wrong. And this is what we look for is this internal fire for actualization. Like I'm trying to become the best version of who I am today and who I want to become, and that usually comes from within. So it's, it's actually, we don't have to do much when you have that already.

[01:07:00] We can do some things in terms of giving you the tools to get better at that and all of that, but it comes so much of it is from the inside and in order to get there. And at least in my opinion, and likely most psychologists opinion, and I may be wrong about that. My personal experience rather is that I had to get over those things to deeply in this state.

[01:07:22] And so much of it was around like, oh, I maybe need a partner that I feel like safe with. I need to have better relationships with my friends and my family. And it took me years to fix those first. Then I felt like I was able to work on this and, and succeed at work. I may be wrong about that, right.

[01:07:41] There's probably, I know plenty of founder friends, even who are like low EQ, but highly successful at doing what they're doing. So there's, there's again like many different ways to skin a cat, but I feel like mastery, I don't know, I may be wrong about this, but I'd love to hear your thoughts.

[01:07:57] Dan McDermott: Yeah, sure. I largely agree with you. I think that finding people who are ambitious and passionate and driven and wanna get better at what they do. And, and we obviously wanna find those people and we do a pretty good job of, I think finding them for our clients, but.

[01:08:16] I don't think we should limit ourselves to saying necessarily that you have to have this prerequisite of a certain level of call it what you want balance health, even confidence. I'm not sure what the right term is for that, but you, you don't necessarily how it's hard to define that somewhere. But I think that, again, going back to culture, if you really truly build an amazing team and I'm, let me be extreme for a second here.

[01:08:41] Maybe exaggerate just for the sake of it. But if you were to look at teams that are just an incredible environment to be around where you show up. Let's say again in a neutral state and you're say, okay, I'm here to do my job and you walk into the room and you genuinely walk into a room of people walking up to you and being like Nim, what up welcome day one.

[01:08:59] Let's go, baby. This is gonna be great. And every day they're just constantly high energy. They're constantly there. It's difficult for you not to be high energy like them. This is just a basic thing about just elevating yourself from an, from an energy perspective. But then if you see people working hard to better themselves and sort of, and you see, you're a sales manager, Mike kind of be like, Hey Mike, what did you do with that CTA.

[01:09:19] I wanna start doing this, or you, you sort of see this in front of you with essentially the experienced people on your team leading by example, it is very difficult for the new person to not pick up those habits, in my opinion. And it's, while culture is a very vague and difficult thing, it's ethereal it slips through your fingers sometimes, but if you can build that by hiring the right kinds of people to, well, I think culture is very much top down, at the beginning in a lot of startups because it's literally the founder, right?

[01:09:47] And if you can create that it's a roundabout way of me saying, I think the founders can often do a great job of creating wonderful culture for that first one or two people. And then those first one or two people can turn around. And if they're empowered the right way can really create an amazing experience for the next round of people to come in.

[01:10:05] And I think that's the special thing about startups, especially at very early stage ones. Yeah. I mean, we don't have to hire anybody, but we could get in somebody with a little bit of wants to put their mark on something. So I agree with you that yes, you should be looking for people who are already as far advanced on that fake pyramid.

[01:10:22] Maybe the Maslow thing. But, for the most part, I think that I would like to think anyway, I would like to view most people as coachable to the point of wait a minute. I can just, I don't have to be, I don't have to be sarcastic and kinda like goofy about this stuff. I can just show up and just be stupidly happy about the fact that it's a Monday, like, okay, interesting.

[01:10:45] If I, we have a thing about also when, when we do live training with companies, we'll go around, we'll get everybody to stand up. We'll get everybody to just kind of be physically in the right space. Get everybody in the right, teach them little routines to again, protect yourself mentally after something bad.

[01:11:01] Put yourself into a good state in front of something good. And then also I think that's sort of surface level stuff for, for that are it's important, but it's surface level. It can, can disappear quickly, but then train them on how to do this for themselves later. Like at the end of the day, before you go to bed, are you happy?

[01:11:19] I remember I interviewed a sports psychologist. She was the coach of the US Women's Indoor Cycling Team and a former gold medalist herself. And,I asked her all these questions about metrics, about looking for, are you weighing your athletes every day? Are you doing all this kind of crazy stuff?

[01:11:34] She's like, whoa, whoa, what are you talking about? I only asked them one question. I was like, no, what what? And she's like, yeah. So I only ask them, can you sit in a. With yourself in silence for 15 minutes. And I, it was the first time this was maybe going back about seven years ago, but it was the first time that I had this like switch go off in my head about this type of stuff.

[01:11:54] And I, up until that point, I had been very much, like you describe yourself early on of just working the late nights and then killing yourself just to be productive. And after that conversation with her, I kinda reassessed a lot about how I was going about my own stuff. And, I think I see this translate over to teams as well.

[01:12:14] Nima Gardideh: Yeah. I mean, first of all, that question is an amazing question. The 15 minutes of silence. 

[01:12:19] Dan McDermott: It's a powerful one. 

[01:12:20] Nima Gardideh: If I were to repeat back what you just said to me, which I really liked, which is, it sounds like you are saying that you can create a culture, an environment, and such that even if I haven't reached that level of wanting self actualization in the way that I described earlier, the environment is positive enough that you can find some form of joy in the process of begging getting better at what your job is.

[01:12:54] Dan McDermott: Let me, let me frame it in another way too. Like, I mean, think about yourself. I mean, I'm projecting here because I'm thinking about myself here, but think of ourselves at, let's say the age of 20 or 22 or 23. I didn't know what I didn't know. And I was very much okay.

[01:13:12] Entrepreneur track and I'm gonna build a business and I'm gonna do all this kind of stuff. Right. And it's in most of the old school training, none of this is really talked about. So it's it's, but increasingly it is, which is great. But if I came into an organization at the age of 23, not knowing stuff, but being open and being generally positive and, and ambitious, and I was given structure around me by people 10 years, 20 years, more advanced than I was.

[01:13:40] I think that, yes, that kind of stuff will absolutely shape how I start to behave, how I start to think, how I start to actually genuinely feel about my job. And if it's a two edge, double edged sword there. If it's not there, if that structure is not there, if that culture is not there.

[01:13:56] I will very quickly learn to do all the bad things very quickly too, because people around me just don't care. Don't talk to each other. Don't smile. so it's, these are things that can be manufactured, but I would argue that that if you give the majority of positive young people with energy, that kind of framework to operate within, and show them why it's important, a lot of people would just be, be happier at their, at, at their jobs and more successful in general.

[01:14:20] Nima Gardideh: And there, it's almost like a gift to your, to those people, because there's this thing called job imprinting. I don't know if you've 

[01:14:25] Dan McDermott: No, I've never heard that term. 

[01:14:27] Nima Gardideh: It sets the stage for your whole career in that it imprints what you expect from people around you, the teams around you, and how things are meant to be.

[01:14:38] There was like an HBR study a couple years ago around it. And I remember reading it thinking, wow. Yeah, I can see how much my first job affected how I built things later on as an entrepreneur. But I only had like a real job for six months before my first entrepreneurial sort of endeavor, but still even then, there was a lot of imprinting, before we wrap up let's let's go.

[01:15:05] Yeah. I think it's a great, yeah, it sounds like we have decently overlapping histories or, or journeys. What is your, so talking about this culture of like trying to make sure we're all collaborative and there's avoiding internal competition in the negative way,

[01:15:30] marketing teams, obviously to some extent are involved or even responsible for some of the leads that get generated for a sales staff. There's two questions I have for you. One is. How do you think the org structure should be done? Like, is there a VP of Sales and a VP of M or a Chief Revenue Officer that like both of the teams report to like, what, what are your favorite org structures there?

[01:15:59] And then if you were to sort of s up like an, an approach or a philosophy that the teams should have collaborating, what is like the, your favorite one there? 

[01:16:11] Dan McDermott: I think one, one common issue. I'll come back to the org structure in a second, but I think one of the most common things that I ask for whenever, whenever a team is onboarded with us, is that,if there's an existing sales team, let's assign somebody to own the copy.

[01:16:28] Who's gonna be responsible on the team to be writing either the emails or the call scripts or the whatever. So we will hand them templates. We will often write with them, but it's very important to have somebody on the team who's able to say, okay, I understand what we're trying to do here. I have the skills to some degree to be able to write the stuff up.

[01:16:49] The reason that's important is that if that person is not there, then essentially the sales team is being handed material from somebody else who does not, who never talks to customers. And that could be the CEO, or that could be the marketing team. That doesn't mean that you guys never speak to customers, but not in the same way in terms of literally calling them up and just having hundreds of conversations every month, thousands even.

[01:17:10] And I think that's the biggest flaw that I see in a lot of the structures is that often when a marketing person, , when a marketer, when a copywriter from the marketing team writes email, copy, they're writing marketing emails, and then giving them to a sales team and saying good luck. And it just doesn't work the same way because we're, we're doing the same general thing.

[01:17:31] And just trying to make a closer relationship with the customer. But we have a specific goal that's a lot more clearer than the marketing team. The marketing team has just a bigger cycle that can send endless touches to somebody. So it's okay. I think the average is something like 37 touches on, on the marketing side before a conversion.

[01:17:47] So on the sales side, we don't have that luxury. We have a couple shots and so yes, you have to be more direct, but you have to have somebody who's able to, able to actually. Give the team, the rest of the team, the right material. So that's number one. I look for somebody to actually own that.

[01:18:01] And it could be an SDR. It could be an AE. I don't really care as long as it's one person to then consistently build better and better material in place at a bigger picture. How to structure the orgs, this shifts as a company scales, right? So if you have just literally a handful of people, five people on your company, it's difficult to say, we need a VP of sales and we need a CMO and we need all these different people to then be the leaders of teams when you just have a handful of people.

[01:18:32] So in that sense, I would, is gonna be a little bit of a non-answer, but bear with me, basically, whoever's heading up the marketing department and whoever's heading up the sales department should at some point be different people and be reporting to the company leadership separately. And then should they be collaborating?

[01:18:51] Absolutely. Should they be meeting with each other? Absolutely. At some point, I see it as a sort of a tree that goes up in two separate ways, but through one, one person on each side and then goes back to leadership. Is that enough of an answer?

[01:19:04] Nima Gardideh: Yeah, I think that, that makes sense to me. I think the collaboration part is just that the part that makes is, is hard to do, but, I found it that some teams that don't have, like, if. There is like a VP Marketing and a VP of Sales let's say, but they go into not to the CEO, but there is like another person whose job is to bring on overall revenue.

[01:19:28] So like a chief revenue officer of sort, yeah. To be a little bit more performance, because there is that one person who is ultimately responsible for the thing, for the bottom line of the business and, or like the top line of business rather. And so they're, they're making sure they're ensuring some level of collaboration, collaboration more than when there's two VPs and they're kind of fighting for resources with, with the CEO. but that may, I don't have enough data points to tell you that that's the right move. 

[01:19:57] Dan McDermott: No, I think the bigger an organization gets, the more likely that kind of structure is necessary. I think, whereas if you're, if you're really in kind of like, let's say, I don't know, this is again, not a great barometer, but like a series Aish, give or take, maybe series a series B preceded, or seed capital, something around there.

[01:20:18] Maybe you're not quite big enough to have the full blown team built out with hundreds of sales people and multiple levels of leadership. Whereas if you're something under 20 people, I doubt you need to have the same level of management structure on top of everybody, basically.

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[01:20:39] Nima Gardideh: Yeah. That makes a lot of sense. Well, Dan, thank you so much for joining me today and this was super fun. I'm excited to get to know you more, yeah, this is great. Thank you so much. 

[01:20:50] Dan McDermott: Yeah, you got it. Great talking to you.

[01:20:52] Nima Gardideh: I don't know about you, but I feel like I could go and build a sales team just by talking with Dan. His insight and strategies really set the bar high. Thank you for listening to this episode and to all of our other episodes we've released. Hint: we have 10 others to binge. Hit that follow and subscribe button to get each episode. All right until next time.

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